The Villa star has been heavily linked with a move away from the Midlands this summer.
Tottenham were leading the race to sign Grealish, 22, however, Chelsea have now emerged as joint-favourites to sign the attacking midfielder.
The Premier League big boys could make a £20m bid for Grealish in the coming days, however, Villa are currently refusing to sell.
And Chester says the England Under-21 international says the Villa players won’t hold it against Grealish if he quits for the top flight.
“I think Jack is the most talented player at the club and deserves to be playing at the very top of the game,” Chester said.
“People forget he is still very young, but we know Villa will be a real threat to anyone in the division if he stays.
“It would be sad to see him go and I don’t know if he will now that the ownership of the club has changed.
“But I don’t think anyone should hold it against him if he ends up going to a top Premier League club.”
Villa were plunged into financial turmoil at the end of last season following their heartbreaking loss in the Championship play-off final against Fulham.
However, new majority shareholders Nassef Sawiris and Wes Edens have steadied the ship after buying out Tony Xia.
The Villans start their Championship season on Monday night, with Steve Bruce’s men facing Hull.